Help Me Choose
Jordan Benjamin

By: Jordan Benjamin on March 8th, 2021

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David Katz



DK:Virtual event and keynote speaker was Chris Voss - Negotiation success is to use a low and slow speaking voice - science shows you will drive a better results
Did you think you would get into sales? What got you there?
In school, as a TA, Dr. Bill Copeland. “You’ll find yourself in a sales role later in life” Was offensive- didn’t know anyone in sales, especially tech/corp sales - Used Car sales 
Thought he would be in law or non-profits 
Wanted something with some more action, some competition and hopped into sale
Why sales? What triggered that?
Robert Scott- research & staffing - spun out of fidelity and sold to partners running it. Now Park Square Exec search in Cambridge, MA - Exec search working on retainer to recruit senior executives and board members. Specifically with VCs and portfolio companies 
Opened a west coast office and Eric Lund, Partner, invite David to come out to SF as a 20-something kid to live out West
Living in the Bay Area hard to not get the software company “bug” working in Tech 
What Skills do I have that could transfer? What product knowledge can I help with?
LinkedIn kept coming up, using it a lot for recruiting efforts.
If You’re in recruiting you’re in sales.  One of the most challenging sales roles in the world.
Selling to the client. Then recruiting for the client. And then sell the candidates on the client. Tons of irrational behavior and emotion
How did you start thinking differently about sales when you moved into sales leadership?
From 2011 to 2016 elevated himself in his sales career from Individual Contributor to Sales leader growing teams of 100+, opening offices around the world and learning. 
Crazy whirlwind period in tech, massive valuations. 
@ LInkedIn as AE, “Say YES”
Back then mantra was Grow Fast or Die Slow -- McKinsey Article
People are trying to be a little smarter with investments today
Anywhere you go there’s incredible opportunity, it’s up to you to capitalize on it. 
Try hard things
Run to the things that people are afraid of or running away from
Mentorship has been powerful for you.  How has that worked for you and changed your perspective during your career?
Lots of misconceptions of mentorship and what it should be.  Many people don’t have mentors today.  Always intentional about seeking out mentors who can help him with what he’s trying to figure out now. 
Mentor = someone with NO skin in the game to bias you or point you in certain directions. Someone you admire, respect and find credible.  When they push you and tell you you’re wrong or things you don’t want to’ll listen
Seek out mentors - rather do that than listen to podcasts
So much of what you read and see in a public setting is BS….when you get behind closed doors they will be more honest and transparent
How do you think about bouncing back from failure?
I have failed 10X more than I have succeeded professionally
The best way to learn and grow is through failure
I personally have a high appetite for risk, there’s no right or wrong.  Sometimes I may make decisions against the data and trust my gut.  Willing to live with the consequences of those decisions
Some things are in your control and some aren’t. Sometimes you will fail
7 months at HubSpot - wanted to see us test more in our interview process is mindset - we were speaking about it and investigating it.  Worked to revamp the interview panel in what we test for. 
Most of the weight I place on to make an offer to someone is based on their mentality and ability to PERSEVERE
I’ll take Perseverance over any attribute all day
Ratatouille 1& 4 year old- rat learns from the chef Anyone can cook; I personally believe anyone can sell.  It’s whether you want to. 
If you want to invest in it, anyone can learn to sell and be successful. Not many people have the mentality or can persevere through some of the lows that come in this profession.
Talk to me more about mindset
Have a naive optimism that things can be better, we can shape things, we can control things, there’s light at the end of the tunnel when you don’t even see it yet. 
Childish naivete and having a positive outlook paired with someone truly having self confidence - not a bravado or arrogance. Having a core sense of anything I want to may take awhile...but I can get there
Inner Confidence comes from growing older and life experience
Every life experience you have helps you become aware of WHO you are
The things that fill you up with energy and drain you
Learn how to play to your strengths, amplify them and have others who can help you fill those gaps
Self-awareness + optimism 
How do you define qualities for exceptional leaders?
Been really fortunate to work up close and further away with some really great leaders
Building teams for BDRs, AEs, SE,s etc. 
Have been able to see lots of different great leaders
Spent time hiring for roles he has never been in.  Hiring SEs and couldn’t do that job, kind of a crazy concept. 
Core things a real strong leader can do:
Best leaders are the BEST LISTENERS. 
Active listening is a challenge in Sales, a lot of folks, early in their career are excited and you just want to talk and talk and talk….and I’m guilty of that all the time. 
Have to be able to LISTEN and UNDERSTAND what’s being said as well as WHAT IS NOT BEING SAID
WIth years of experience you see patterns from certain types of folks, you try and interpret their problem, or the prospects/customers communicate a problem but isn’t what is the real problem and it will take you time and further questioning to elicit the right information to understand the real problem
Active Listening
Assess Individuals -understand their personas and profiles - you will see these in repeating orders the more hiring you do.  This will influence what you communicate with them, how they will respond, how they want to engage. Learn who to surround yourself with and who to surround other people with
Know how to build the best team of the best leaders that complement each other and work well together
Be YOURSELF- be genuine - it takes a long time to get comfortable in your own skin, with your weird flaws and idiosyncrasies - it takes some time to get there. People that are authentic and genuine and vulnerable can admit mistakes and failure -- Psychological Safety
Not easy to be yourself in conversation with prospects/customers. But if the perception doesn’t meet reality, the chink in the armor will be seen and you’ve lost all credibility! 
How do you feel about bringing the whole human to work?
Not sure showing up fully was taboo, but early in your career it’s harder. The older you get the longer you’ve been in a chosen career, the less you care about. The things you care about you care a lot more. 
Some of the things I put emphasis on early in my career, were so silly. 
You look back and reflect 
Early in your career it may be about- Title, Role, responsibility, how many people do you have reporting to you and how you measure your success against others. 
There’s momentum to be more comfortable talking about mental health.  People never felt like they were ready to talk about it.  Someone breaks the seal and everyone else can open up further. 
How do you balance home & work and juggle all those balls. It’s really hard to, once you know yourself better, a lot of things you would have chased early on were silly. 

As you achieve the goals you set-up for yourself and realize you aren't’ as fulfilled, is because you put the wrong emphasis on the wrong things. 
Other company offering big title, promise and dream.  
The grass is brown everywhere. There are challenges and opportunities and every company. 
Don’t solve for title 
Seen such talented people go to tier 2 or tier 3 companies because they were chasing titles. I used to do the same things but at some point you realize you aren’t happier. 
You were solving for the wrong shit. 
This role, the company, the culture, probably the most satisfied and fulfilled I’ve felt professionally in a while. Not to knock  previous companies, they were incredible and learned a lot along the way 
Working with a smaller team, just really focused on North America, it’s a smaller role than I’ve had in a long time and took a handsome pay cut. Because he realized through hardship himself personally. Having a new family, young kids, support his wife in her professional development. 
It’s really hard to fulfill yourself if you can’t be present. 
I want to do work that is insanely fulfilling and want to be at home at night for my family. 
Love winning or hate losing?
Hate losing
Think about goals personally and professionally all the time. Everyone goes about charting progress differently. Realized that focusing I can have more Longer term goals and less short term goals, I get more accomplished. 
Fewer goals short term gives you the ability to accomplish more long term goals.
What does success look like to you?
Happiness and fulfillment
Favorite interview question?
Stolen from Peter Thiel;
“What’s one thing you know to be true that nobody else would agree with you on?
David Katz on LinkedIn

About Jordan Benjamin

Jordan is the founder of My Core OS. After spending years in sales, working with sellers and studying peak performance he found an opportunity to help sellers level up to not only build peak performance at work, but to also create harmony between work and life so you can sustain performance over the long term.